Sodium Hydroxide → HCID 54673216, compound

HRID 563600Notes

Reaction equation

HRID 563600 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][NH:24][C@@H:25]([CH3:34])[C@H:26]([OH:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[OH-].[Na+]>CO.C1COCC1>[OH:33][C@H:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C@@H:25]([NH:24][CH2:23][C:14]1[CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:18][C:13]=1[C:7]1[C:8]([O:11][CH3:12])=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([OH:35])=[O:2])[CH:6]=1)[CH3:34]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 66607791HCID 66607791, compound

Product 1

HCID 54673216HCID 54673216, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

{2′-[((1S,2R)-2-Hydroxy-1-methyl-2-phenyl-ethylamino)-methyl]-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid methyl ester (0.021 g, 0.04 mmol) in MeOH (0.33 mL) and THF (0.4 mL) was treated with 1N aqueous NaOH (0.1 mL) and stirred at room temperature for 4 hours. Analytical LCMS showed that some starting material was still present, so additional 1N aqueous NaOH (0.05 mL) was added, and the reaction was stirred at room temperature overnight. Analytical LCMS showed that starting material still remained, so additional 1N aqueous NaOH (0.1 mL) was added, and the reaction was stirred for 4 hours. After work-up with CH2Cl2 and 1N aqueous HCl, the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. stirringthe reaction was stirred for 4 hours
  3. dry with materialAfter work-up with CH2Cl2 and 1N aqueous HCl, the combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-350c9a798c264beba4e8b0f75813fb58
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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